Collect. Czech. Chem. Commun. 1983, 48, 2693-2700

Preparation of 3-deoxy-3-fluoro-D-mannose and corresponding hexitol

Miloslav Černýa, Jitka Doležalováa, Jindra Mácováa, Josef Pacáka, Tomáš Trnkaa and Miloš Buděšínskýb

a Department of Organic Chemistry, Charles University, 128 40 Prague 2
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reaction of 1,6 : 3,4-dianhydro-β-D-altropyranose (I) with potassium fluoride in hot ethylene glycol gave 1,6-anhydro-3-deoxy-3-fluoro-β-D-mannopyranose (II). On acid catalysed hydrolysis or acetolysis of compound II 3-deoxy-3-fluoro-D-mannose (VIII) or its tetra-O-acetyl derivative VII, respectively, were obtained. Reduction of compound VIII with sodium borohydride gave 3-deoxy-3-fluoro-D-mannitol (IX). The structures of the mentioned compounds were proved by 1H NMR spectroscopy.